Hiring Your First Product Manager

As a technical or product-focused CEO/founder of a growing company, a challenge one eventually faces is making that first product manager hire. Like most founders, there’s a good chance that you’re seeing ongoing challenges balancing the ever-increasing workload as CEO and starting to feel that sense of distance from the product as the needs of sales, marketing, hiring, and more pull you away. You might be wondering how you can spend more time on what you love, the product, while recognizing as CEO you must grow the strength of the organization while also focus on the contributions that you can make uniquely from the CEO role.

This is where making the first product manager hire is necessary and also a unique challenge. Most of the time, this hire is postponed as long as possible. You can cover-up for this missing resource with additional late night mails, some extra last minute meetings, and so on. The time this really hits home is when feature work or decisions turn into re-work or re-thinking. That’s the sign it is time to hire some help. Engineering resources are precious and timelines are always tight—being the founder-pm-bottleneck is no way to iterate your way to product-market fit.

The short answer to this next step is two-fold. First, at an emotional level this is extremely difficult for most every founder (btw, in a big company if you are starting a new product team it turns out this same dynamic applies). It is likely you will talk to quite a few candidates and no one will ever seem quite right. Second, you are going to have to trust your team a great deal on the fit and in doing so adjust your own approach to product management as part of the on-boarding process.

Every situation will be unique and there is no single rule for what type of skillset, experience, or seniority will be right for you and your company. The most important thing to think through before you start the process is to agree between your co-founder(s) and team on the profile of the role you wish the new PM to play in the organization.

Traditionally this would be framed along the lines of a job description:

Seniority. Are you looking for a VP, Director, Lead? Most typically you start here but these descriptions might fall short of really defining the role and so you end up seeing a lot of candidates.Domain. Perhaps you are looking to fill in a specific technology background as part of this hire? As the product evolves you might be expanding into product areas that could use additional strength from product management. The question is really how much this will change the bottleneck you might be seeing.Skillset. Are you looking for a candidate with more of a design, project management, or engineering background?

Each of these are examples of necessary but not sufficient criteria in kicking off the search for your first product manager. Because the first product manager hire is so unique for a product-focused founder, it is worth offering a framework or characterization of the role that you might start with.

Once you arrive at characterizing the role, then you are in a better position to narrow the search by more traditional experience and skills descriptors. Each of these below can work with the key being clear on hire and in management what the expectations are for the new product manager.

Extra hands. Most every founder I speak with starts the description of needing an extra set of hands, eyes, ears—someone to offload some work to, follow-up, track down, etc. This is often a positive stop-gap and can certainly work short term. Medium to long-term it can also starve you of the opportunity to grow the organization or might mean you set yourself up for yet another product management challenge down the road. If you go with this approach then the important thing to watch is that you did not solve you bottleneck problem by just moving it to another person or adding a level of bottleneck-indirection.

Process chief. Are you looking to offload the unpleasant or less intellectual aspects of product management such as the details of tracking, documenting, and other “process” issues? It is quite natural to be very narrowly focused in hiring the first product manager to want this set of skills added to the team. It isn’t uncommon for engineering to also seek this addition. The good news is this is almost always helpful. The challenge is it also adds another person to the team for the short term but might not really reduce the load or bottleneck but could unintentionally add friction to the process. A careful balance is required.

Apprentice. Many times the goal of bringing on the first product manager is to reduce the risk of hiring a senior or experienced person and going with a relatively junior hire and working to grow him/her into the role that you actually need. This can often be the most comfortable approach for the team because there’s a clear view of who the boss is and relatively clear expectations with the new PM. Generally the challenge can be down the road when you bring in more product managers and have to decide if the apprentice is “senior enough”. To avoid this challenge the best thing to do is really put in place a true training and growing situation. You need to provide the right level of responsibility and feedback/mentoring. Sometimes the difficulty is in hiring at this level but expecting too much, too soon.

Mini-me. Another model I have seen is searching for that first PM that is a reflection of your own skillsets and experience—a mini-me. For many this younger-sibling approach can be comfortable and easy to model and understand. It is a matter of finding the candidate that shares your product point of view and vision, and then a way of getting it done. The interesting challenge with this approach is not the way it works, but the way it might not work. Will the new PM amplify not just your strengths but your weaknesses? Will this miss out on the chance to being more perspective, diversity of thought and approach, or new ideas into the team? Are you being imitated or copied?

Successor. The most difficult or bravest first PM hire is to hire your successor. In hiring this person you’re bringing on a person who will simply be the final voice in product management. This is a scary approach and depending on the direct responsibilities you have and where you are in the product-market fit journey this might be the best approach for you and the team. The challenge I’ve seen most often with this first hire is that the seniority level doesn’t quite match the organization yet. The new hire’s first step is to build out a team and bring on more people. This might be exactly why you’re bringing on the person (just as when you bring on less familiar functions) but generally isn’t the case for product management as most often the first hire needs to be hands on and will buy you some time or runway. On the other hand, often the right candidate comes along—one who has the right level of person contribution, domain knowledge, and scale experience—and that might make for the right fit.

Of course hiring the person that fits this description as well as all the right product skills could turn into a unicorn hire, so definitely be careful about over-constraining the challenge. Of course, hiring is just the first step. As you onboard, assign and delegate work, and manage a new product manager you will also need to be incredibly deliberate in your own evolving role in product management. All too often the most-fitting hires can run into challenges when there is a mismatch between intention and execution of product management responsibility.

One word of caution. If you are concerned or even “afraid” of hiring a strong product person with a point of view, perspective, or just streak of stubbornness then think for a moment. Are you labeling the person a poor fit for “culture” or are you actually more concerned that they might make your own personal transition more challenging? If you’re working to always bring on strong people, don’t compromise at this juncture.

Hiring the first or early product managers for technical/product focused founder(s) is always a big step and a difficult one. When done correctly it can be a positive and rapid accelerator for engineering and a positive for the company overall as it makes room for you as that leader to focus on the work you can do uniquely.